Family-friendly holiday rentals in Chincoteague Bay

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chincoteague Bay family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Apartment in Bethany Beach
4.93 out of 5 average rating, 298 reviews

Sea Colony Premier Family Resort

DioneRating, 5 stars1 month ago
Love staying at Marie's condo in Sea Colony. This was the first time that we were in Bethany Beach in early May in many years. It was fun seeing the community get ready for the upcoming season. Marie is proactive and responsive. Her place is perfect for 2 people. :)
Guest favourite
Apartment in North Wildwood
4.96 out of 5 average rating, 105 reviews

Beach block condo, pool/spa, 2 parking, 4 bdrms

MichelleRating, 5 stars3 months ago
The house was very spacious and accommodating. Great location near the beach and boardwalk. The host always responded quickly and was very easy going. We would definitely stay here again.
Superhost
Apartment in Bethany Beach
4.89 out of 5 average rating, 176 reviews

Beautiful Beach-View Condo

EricaRating, 5 stars2 weeks ago
We loved Raj’s place! We have two young children and his place was fully equipped to entertain them with books, toys, etc. Best Airbnb we have stayed in so far 😊
Superhost
Townhouse in Bethany Beach
4.92 out of 5 average rating, 110 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

ValeriaRating, 5 stars11 months ago
Sherri’s place is awesome and the community and surroundings are beautiful. The kitchen is furnished with everything you need for cooking. The deck is such a plus, with the view of the pond and the ducks, as well as the private little beach. The community is very friendly and walkable, and the different options for pools were very fun for us to explore. Taking walks in the morning was amazing. It is very close to Bethany “downtown” and 6 min drive to the beach. You can also walk or take the tram. I had a great time with my kids and would definitely recommend and come back!
Superhost
Home in Annapolis
4.87 out of 5 average rating, 179 reviews

Charming Annapolis Water View Home

ManningRating, 5 stars1 month ago
This house is uncommonly beautiful. There is something in every space worthy of contemplation whether it is coffee table in the living room that has a turn of the century industrial feel to the lacquered kitchen countertop that has sealed in the natural beauty. I spent the weekend in awe of its intricacies. I was in town for a wedding with my family, but noted how the whole house including the outdoor space included everything a beachfront house would have to enjoy an extended summer vacation for the whole family. Outdoor space was well equipped for outdoor activities and entertainment with fire pits, grills, hot tub, a plugin cooler for outdoor use. I only wish we’d been better suited to enjoy every aspect of the amenities provided. My favorite thing about this place was the view of the Chesapeake in all of her glory on full display from the living room window. Delightful.
Guest favourite
Home in Severn
4.88 out of 5 average rating, 170 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

SamihahRating, 5 stars1 week ago
This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!
Superhost
Home in Rehoboth Beach
4.95 out of 5 average rating, 105 reviews

Amazing Bay Vista Beauty with Private Pool!

RobertRating, 5 stars10 months ago
We have stayed here many times & wouldn't consider any place else. The home is very well furnished. The kitchen is very well supplied. It is minutes from Lewes, Rehoboth Beach, and Delaware State Parks and provides a very large swimming pool + hot tub. And you can't beat it for privacy which is very important to our large family. I'd give then place more stars if they were available.
Guest favourite
Flat in Arnold
4.94 out of 5 average rating, 175 reviews

Celebrate Summer by Your Private Pool

JennaRating, 5 stars9 months ago
Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Family- and pet-friendly home rentals

Guest favourite
Cottage in Deale
4.82 out of 5 average rating, 181 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

BobRating, 5 stars4 weeks ago
Shawn's place is great! It is well-cared for and has everything you need to enjoy the indoors and the outdoors. The views of the water are beautiful and you can spend a lot of time watching the different birds. Getting there is easy and not far from restaurants and grocery stores. Shawn makes you feel special and wants to ensure you have a wonderful stay. Hope to go back soon.
Guest favourite
Cottage in Lewes
4.87 out of 5 average rating, 201 reviews

BnB’s Dog-Friendly Cottage

SydneyRating, 5 stars1 month ago
Jacki's home was so lovely and perfect for a weekend getaway with some friends. We brought our dog who absolutely loved the fenced-in yard and extra loved the mountain of toys stocked in the house!
Top guest favourite
Home in Lancaster
4.99 out of 5 average rating, 234 reviews

Rivah View

PeteRating, 5 stars2 months ago
Relaxing, well-kept property and house with a view. Plenty of good food in next town over. If you haven't been to Northern Neck, stay here and enjoy some peace and quiet.
Guest favourite
Guest house in Lewes
4.95 out of 5 average rating, 190 reviews

Very private and cozy, Country Cottage

TrevorRating, 5 stars2 days ago
This was the perfect getaway for my family and I. Zully was a great host and incredibly friendly!
Superhost
Flat in Silver Spring
4.92 out of 5 average rating, 444 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

AndrewRating, 5 stars1 month ago
Very responsive host. The side yard is very nice for people with dogs that travel. Location is very nice but DC traffic during rush hour can be rough but this can be planned for. Would stay again.
Top guest favourite
Home in Greensboro
4.97 out of 5 average rating, 155 reviews

Cozy Riverside Cottage in the Woods

ChuckRating, 5 stars1 month ago
Just a wonderful location. Very private and the property is beautiful. The house was well-equipped; it included a couple of kayaks that we used on the Choptank River, where we saw ospreys, eagles, and even a beaver. The beds were comfortable and the decor and other items in the house were very interesting. We likely will be back some time.
Top guest favourite
Flat in Lexington Park
4.97 out of 5 average rating, 568 reviews

Historic St. Mary's City, MD

AnnaRating, 5 stars5 days ago
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.
Guest favourite
Flat in Middle Township
4.89 out of 5 average rating, 212 reviews

Stone Harbor Water Views

MRating, 5 stars3 weeks ago
We loved staying at Steve and Louise's beautiful property. Watching the sun rise and set over the tidal wetlands was magical, and there were many amazing birds. The fenced yard was great for our dog. The interior had good natural light, which is unusual for a ground floor unit with a balcony over it. The bed was extremely comfortable. Steve was very nice, and made sure to check on us frequently to see if we needed anything, and stopped by to chat a number of times. As listed, the indoor shower is small but the outdoor shower is much larger. I used the outdoor shower and the water pressure was great. It might be difficult for someone elderly or with mobility disabilities because it's a little hard to balance on the sloped slippery wood. The location is perfect - between Stone Harbor and Cape May Courthouse so it is convenient for necessities, but easy to get to the beach. We really enjoyed our stay and hope to come back again.

Family-friendly home rentals with a pool

Guest favourite
Cabin in Saint Michaels
4.99 out of 5 average rating, 110 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

SheriRating, 5 stars1 month ago
Great place for a getaway! St. Michael’s is a wonderful town and so easy to get to from this lovely place! Was perfect location for our family ladies trip- plenty of space and just a quick trip down town to the shops and restaurants! - I think we’ll be back!
Guest favourite
Apartment in Rehoboth Beach
4.94 out of 5 average rating, 114 reviews

Cozy Condo on Silver Lake - Walk to the beach!

DeborahRating, 5 stars5 days ago
We have two elementary aged kids and the location was perfect for us - we were next to the pool, and two playgrounds and the basketball and tennis courts were a few minutes walk away. We enjoyed the wildlife and quiet but were able to go into town and visit the boardwalk easily. Thank you for a lovely stay Sue!
Superhost
Apartment in Rehoboth Beach
4.89 out of 5 average rating, 146 reviews

Right on Silver Lake walk to the beach and town!

ChrisRating, 5 stars3 weeks ago
Pleasant surroundings, nice quiet location with lovely view. The well equipped kitchen went mostly unused due to myriad eateries within walking distance. Parked our vehicle and chose not to, and never needed to use it during our stay. Oh, and if you're into turtles the Turtle Bridge is aptly named. Good experience overall, would happily stay again.
Top guest favourite
Apartment in Ocean City
4.96 out of 5 average rating, 152 reviews

Waterview, Steps from Beach, Linens Included!

CherylRating, 5 stars9 months ago
Great host! Would definitely stay here agsin
Guest favourite
Apartment in Ocean City
4.91 out of 5 average rating, 309 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

CarolynRating, 5 stars1 month ago
I had absolutely the greatest time the most relaxing experience I’ve had in probably 20 years . Kathryne was so amazing to work with!! And the home was lovely! I can’t say enough good things!
Top guest favourite
Home in Rehoboth Beach
5 out of 5 average rating, 195 reviews

Beautiful Beach House in Rehoboth

RebeccaRating, 5 stars1 week ago
Had the absolute best time staying at this gem. The house is stunning and Autumn was a fantastic host! The house is spacious and open. It was exactly as described but better. We couldn’t have been happier. Will definitely be back!
Guest favourite
Home in Rehoboth Beach
4.99 out of 5 average rating, 126 reviews

Secluded beach beauty with private, heated pool

BennyRating, 5 stars9 months ago
This is a great property! The house is gorgeous, the grounds are clean, kept and very private. The house was fully stocked with kitchenware, pool accessories, & decorated tastefully. A lot of delicate artwork and intentional decor- (if traveling with a young child, one needs to watch them closely :) Re: the beds- my 7 year old described it as “sleeping on clouds!” - very comfy! The area is close (2-3 min) to outlet shops and a bunch of restaurants on Costal Highway 1 and about a 6 min drive to the Rehoboth pier. It’s also a central location to other neighboring beach towns.
Top guest favourite
Apartment in Rehoboth Beach
4.98 out of 5 average rating, 201 reviews

Comfy and Convenient 2 bedroom/2 bath condo

KerriRating, 5 stars2 days ago
Jane was a great person to work with! She was very responsive to my questions and concerns. She was also very supportive with my daughter and her friends visiting the beach together! Their little get away was one that they will always remember! Thank you

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